Finally decided to take my Logitech RumblePad 2 out of storage and hook it up to this machine. I bought this gamepad around 2005 or so, and have kept it ever since. It still works fine to this day.
I have an old version of the Logitech Gaming Software (lgs460enu.exe) which can be installed under WinME and probably Win98SE too. It even has preset profiles for some Win9x era games like Tomb Raider 3 and Need for Speed: High Stakes.
The gamepad worked great with NFS:HS, and even force feedback was enabled and functional out of the box. The rumble effect was a bit too strong by default, but thankfully, you can fine tune it using the in-game controller options. I imagine it was designed for Microsoft and Saitek's force feedback joysticks from that time period, and probably feels much nicer on those devices. Anyway, I really enjoy playing racing games using the gamepad's analog sticks. It feels much more natural to me than using the keyboard.
That said, this gamepad really shines with PlayStation ports like Final Fantasy 7 and 8. It's possible to set up the game's controls to perfectly match the PlayStation layout. This is great for people who have played those games on consoles and have tons of muscle memory associated with that controller. And with some manual tweaking, you can map the analog stick for movement, while still using the D-Pad for menu navigation. Absolute perfection!
Lastly, I tried a couple of DOS games as well (from within the WinME DOS prompt) and they worked fine too. Both Tyrian and Descent correctly detected the gamepad and could use it without any additional tweaking. I do have a CH Flightstick for DOS gaming, but it's nice to know that the RumblePad 2 can be used as an alternative in some cases.